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“What do I say?”

How to start a conversation with a colleague you don’t know

Have you ever walked up and introduced yourself to a colleague whom you’ve never spoken to before and felt a bit awkward? Suddenly, fears from your early teenage years rush through your body: “will this person reject me?” “How will I survive?” Don’t beat yourself up over those feelings; they’re natural...except for the extreme extroverts out there :-)

All you have to do is ask if the person has a few minutes to talk (or a “remote coffee”). If the person asks why, casually explain, “It’s important for me to know who my colleagues are.” It’s hard for a working professional to criticize that.

The worst thing the person can do is tell you that he/she doesn’t have time. And that’s okay. Don’t take it personally. It could be because the person is very shy, or not feeling well, or in a rush to get to the next meeting. We’ve all been there ourselves. No matter what, the fact that you have established some contact is a great first step. Often the person will suggest talking another time, in which case you can propose a couple of alternative times. If not, it is highly likely that the person will reach out to you when it suits him/her. Remember, we’re social animals.


When the person answers, be sure to listen closely to what he/she says and how he/she says it. Again, your purpose is to get to know the person, so listen for clues regarding what the person cares about and ask follow-up questions. Warning: some people have difficulty explaining the details of their role, which is a sign that they don’t know exactly themselves or are frustrated with their current work situation. My advice is to switch topics.

Remember, this is a conversation, not an interrogation. So, be sure to share some information about who you are and what your role is. Balance and variation are important in a conversation. It’s good for the other person to know something about you as well. Otherwise, it’s not really a relationship.


A simple story structure

  1. A Challenge you faced

  2. A Choice you made to overcome that challenge

  3. The Outcome of making that choice


Values – Why? How?

  • Values are a person’s core beliefs that guide his/her decisions and actions. You can see a person’s true character (values) in how he/she acts under pressure. The value of Bravery can be seen when a person takes a risk that might lead to failure or embarrassment. The value of Integrity can be seen when a person shares his honest opinion, even if it’s unpopular.

  • How to choose a value for your story:

  1. Ethical – look at the best examples of how people behave in your organization, behaviors your mom and dad would be proud of. Frequency – look for a behavior that you see in many of your colleagues. It doesn’t have to be a behavior that everyone demonstrates, but there’s enough frequency that you see a pattern

  2. Successful outcomes – look for behavior that leads to long-term business success.

  3. Value – Try to identify the value that lies behind that behavior (e.g. teamwork, passion, honesty, etc.)

  4. Genuine – Make sure you are choosing this value because you firmly believe in it—not just because it sounds nice—and you have many examples of it from your life.

  • You can learn even more about values in the post series on Leadership

How to follow up spreads

Share a Story

One of the most powerful ways to connect with a person is through storytelling. Most people will forget the facts about where you’re from, what you studied, or what your previous job was. But they will remember the stories you tell. Why is this?

First, stories give the person a glimpse into your life that show your humanity, that you are a person and not just a colleague, which makes you more relatable. Second, stories are “stickier,” more memorable, than facts alone. Third, stories show your character, your trustworthiness. So how do you tell a good story?

The best stories portray you (the main character) in some sort of challenging situation, in which you were forced to make a difficult choice—a decision that requires self-sacrifice, or an action that requires hard work. Ideally, the choice you make in the story should lead to a positive outcome in the end (a “Hollywood” ending).

*sidebar 1*

Stories like these resonate with people because hearing about the challenge you (the main character) faced affects people emotionally, but still leaves them feeling positive. Remember, you’re getting to know this person for the first time, so you don’t want his/her first impression of you to be a sad story.

To truly connect with your colleague, there are three important aspects in your story to think about.

First, your story should be relevant for the current conversation: talking with a colleague about your careers and backgrounds. You may have an amazing story about your standing up to a bully in middle school, but if it has no connection to work whatsoever, your colleague might be a little confused about why you are telling it. So, make sure your story somehow parallels a situation at work.

Second, it is important to tell a story about a struggle that most people in your organization have gone through themselves. This way, your colleague can relate to your struggle on a human level.

Third, the difficult choice you make in order to overcome the challenge in your story should reveal one of your values. Ideally, it should be a value that many of your colleagues have as well (e.g. bravery, integrity, trust in others, etc.). Connecting with a colleague through a shared value forms a strong bond between the two of you.

*sidebar 2*

So, what do you base your story on? Make a list of several events throughout your life that show you making choices according to the value you have selected. Then narrow the list down to one story based on which one is easiest to tell and easiest to understand (in addition to all the criteria above).

Write a draft of your selected story according to the Challenge-Choice-Outcome structure mentioned earlier. Be sure to end your story by explaining that you see this behavior in the organization and that you are proud of it. You might add that this is the reason you decided to work for the organization in the first place (if it’s true).

Be sure to practice. Practice telling your story so that you can give a short version (30-seconds) or a long version (60-seconds), depending on how much time you have with your colleague.

You can learn more about storytelling in the guide post about Leadership.



Do I have to remember everything?

You may have been frightened by the suggestion to ask follow-up questions a week later. For many people this is difficult, due to challenges with memory. Just remembering someone’s name can feel hard, let alone the fact that his wife was going to have surgery. This is okay. There are a lot of people out there who struggle with this. The best thing you can do in such a case is to write the information down somewhere (afterwards of course). You don’t need to record everything, just the highlights: name, role, background, family, interests, important events. Doing so has two benefits: it will increase your listening skills when talking to people, as well as increase your ability to ask follow-up questions. Some people may feel weird keeping a “database” of their colleagues, but if your intention is to build relationships and a community, there is absolutely no reason to feel bad about using a memory aid.

Your colleague’s story

Don’t expect your colleague to have a personal story ready at hand. This is very uncommon. However, this certainly doesn’t mean your colleague doesn’t have stories to tell. Everyone has a lifetime of great stories, and there is a lot that you can do to elicit those stories from your colleague.

The reason for doing this is that it helps you build a stronger connection with your colleague. Not only will you see your colleague on a deeper, more human level, but by getting your colleague to tell you a slightly more personal story, rather than just reciting his/her CV, the conversation becomes more memorable from him/her.

This in now way means you should force a story out of your colleague. It’s more of a gentle coaxing. And it’s all about the questions you ask.

When you’re colleague starts to tell you about his/her role in the organization, be sure to ask about his background. Some people do this automatically, but it’s good to ask, just in case

Listen carefully for what part of your colleague’s background he/she chooses to focus on. This often is an indication of what the person prioritizes. Some people talk about family, some talk about education, some people talk about career. Whatever the person chooses to focus on, ask follow-up questions (e.g. What lead you to make that decision? How did that impact/influence you? How did it feel? What was the outcome?). Follow-up questions show that you are listening and interested in the person.

Sometimes, at this stage, the person may already tell you a story. If not, some good questions to encourage som storytelling, “What experiences are you the most proud of?” “What experiences changed your outlook or mindset the most?” Notice that these are not “yes or no,” questions. By not asking “yes or no” questions, you increase the likelihood that the person will give you a more detailed story. It’s also important that you connect these questions to whatever the person has been speaking about. They shouldn’t seem like prepared questions.

If the person seems to enjoy telling the stories, it’s always good to ask for details (e.g. When was this? Who else was involved? What exactly did you do? etc.)

One more question that’s important to ask is either “Why did you choose to work at this organization/company?” or “What makes you most proud about working here?” These kinds of questions have two purposes: they elicit a positive emotion, and they shift the focus to the community that you and the person belong to.

As mentioned earlier, your questions shouldn’t feel like an interrogation. They should all come from a genuine interest. Keep track of time. Even if the person is happy to share a lot of information with you, you don’t want to take up too much of his/her time. You also want to leave some time to tell the person about yourself. Although there’s no need balance it 50/50.

The amount of time it takes for you and your colleague to both share information about your respective roles, as well as share stories about your backgrounds can vary quite a lot. People can be extremely different in terms of how much they talk, how much personal information they are comfortable giving to someone they don’t know very well, etc. Just because some gives brief answers, it doesn’t mean he/she isn’t interested in talking with you. That might just be his/her personality.

However, the person’s body language can give you a lot of information about whether or not he/she is growing impatient and would like to end the conversation. So pay attention. You never want the other person to feel trapped in a conversation. Many people are too polite to say anything, so you want to give him/her a way out. It is always good to stop and ask if he/she has a bit more time or if he/she needs to end it here. The more you do so, the more his/her motivation to speak with you will increase—now and in the future. If your colleague sees he needs to end the conversation here, DON’T WORRY, this happens. People can be quite stressed at work and it doesn’t mean the conversation was a failure in any way. It may just mean he/she has a lot to do. Thank the person for taking the time to talk, say that it was nice to get to know the person a little, and wish him/her a good day. On the other hand, if your colleague says he’s/she’s happy to keep talking, then feel free to continue.


What To Ask about

How do you spend most of your time?

The next step in getting to know the person better is to ask “How do you spend most of your time?” (LL) This question gives the person a lot of freedom regarding what topic to talk about, how general or how specific to be, as well as how much detail to give. In most cases, when you ask people how they spend most of their time, they will be happy to tell you, because the question allows them to talk about something that they want to talk about, which means it’s usually something that they care about. The person may tell you about a work project that he/she is currently working on, a favorite hobby, or his/her family.

Listen carefully to the details, as they can tell you a lot about who the person is: his/her background, interests, goals, etc. Be sure to ask follow-up questions: What does he/she love most about the job? How long has his/her daughter been playing basketball? etc. This shows the person that you’re genuinely engaged (as you should be) and that you are interested in him/her as a person.

Again, don’t turn it into an interrogation. The person should get to know who you are as well. Often the person will eventually ask you to tell them more about yourself. Be sure to share whatever is most important to you (a work project, your family, other passions).

Remember, this is a chat, so don’t overwhelm them. I always think it’s good to default on the side of ending the conversation too early, rather than too late. The main reason for this is because the other person may be too polite to end the conversation, and if he/she feels that you have taken too much of his time, they may steer clear of you in the future. On the other hand, if you end the conversation a bit too early, you leave the person wanting to speak with you more (either because they just enjoy speaking with you, or because they want to hear more about what you are up to).

Remember, the main reason for these conversations is that it’s much more pleasant to work in an organization where colleagues spend a bit more time getting to know each other and feel a sense of community, that you are achieving something together. The next time, someone invites you for a cup of coffee, think twice before saying no, or at least suggest another time.



The most important part in building a genuine relationship comes not in the first conversation, but in what happens afterwards. People are so used to “small talk,” in which others politely ask them about their job and what their interests are, that they aren’t blown away by good conversation skills. What truly builds trust with people is how you follow up on the conversation.

Let’s say in the first conversation you have with a male colleague, he mentions that his wife is going to have surgery in a couple of days. If you see him a week later, you should ask “how did your wife’s surgery go?” This shows the person three important things about you as a person: that you were listening to what he said in the first conversation, that it was important enough for you to remember, and that you cared enough to ask about it.

It doesn’t even need to be as major as surgery. Maybe a female colleague mentions in the first conversation that she will be giving a presentation at a conference. All you have to ask the next time you see her is “how did your presentation go?”

The point is that by following up with your colleague, you show that you are genuinely interested in him or her as a person, that it wasn’t just small talk. People are truly impressed by this because it’s not so common at most places of work; it’s only common with family, close friends, or other strong communities.

A second benefit of following up this way is that you role model a behavior that spreads. When your colleague here’s you ask about her presentation, it will not only increase the likelihood that she behaves the same way about you, it will also increase the likelihood that she behaves this way towards others. The reason for this is that by showing your colleague that you care about her as a person, you are sending a positive emotion. Research in social psychology and neuroscience shows that emotion is contagious* (S. Johnson, Ashby, Isen). Your colleague may not ask another colleague about how his presentation went, but your colleague is more likely to be friendly, cooperative and helpful towards other colleagues. This strengthens the community.

You may not always hear something from your colleague that you can concretely ask about at a later time. That’s okay. Just ask the questions that you didn’t have time to ask the first time. Maybe new questions have come up. It’s also important to vary the topics of discussion, adding different layers to the relationship. Not all questions should be “getting to know you” questions. It’s good to ask more casual questions about the person’s day, weekend, current events, etc.

Relationships are built over time, through a series of conversations—long and short, serious and casual. While it is important is that you move the relationship forward, don’t feel rushed. Borrowing from the gardener metaphor again, you can’t force a plant to grow faster. It takes time. It’s also important not to judge yourself. The purpose here is not to become a master conversationalist, or the person that everyone wants to talk to at a party. The purpose is to build genuine relationships. That’s less about skill than about intentions.

In fact, the strongest relationships are built on more than conversation alone; they’re built on shared experiences and shared struggles. This is why relationships are so intertwined with community and how well we work together (see Organizing to Influence). Relationships are the foundation of a strong community and good collaboration, and a strong community with good collaboration improves relationships.

*Sidebar 3*

Reflection Questions

  • When can you schedule time to talk with colleagues and get to know them?

  • How can you do this with remote colleagues whom you won’t bump into?

  • What can you do to make this into a habit, so that it becomes part of your regular work routine, not just a one-time effort?

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